Description
L-(−)-Fucose is a deoxyhexose monosaccharide found on N- and O-linked glycans and glycolipids of a wide variety of organisms.
1 It can exist as a terminal modification of glycan structures or serve as a point of attachment for adding other sugars.
2 In humans, L-(−)-fucose plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.
1
Chemical Properties
White Solid
Occurrence
L-Fucose exists in nature in various biological niches. A major natural source of L-fucose is the brown algal polysaccharide fucoidan. It is also present in the polysaccharides of tragacanth, potatoes, kiwi, soybeans, varieties of wing peas, canola and other plants.L-Fucose is a minor component in plant cell wall polysaccharides, specifically rhamnogalacturonan, xyloglucan and also arabinogalactan proteins that are involved in plant cell elongation.
Uses
L-Fucose (6-Deoxy-L-galactose) is used in studies of fucoidan polysaccharide containing glycans. L-Fucose is studied as a glycan modifying carbohydrate that generates antigenic sites recognized by IgE antibodies. L-Fucose is used as a substrate to identify, differentiate and characterize enzymes such as the fucosidase(s), l-fucose isomerase(s) and L-fucose dehydrogenase(s). L-Fucose may be used to study organelles, bacterial microcompartments, involved in the degradation of plant and algal cell wall sugars. L-Fucose may be used as a reference compound in rare sugar identification and analysis.
Uses
L-Fucose was isolated from seaweed.
Definition
ChEBI: The pyranose form of L-fucose.
Reactions
L-Fucose is oxidised by the enzyme L-fucose dehydrogenase in the presence of nicotinamide-adenine dinucleotide phosphate (NADP+) to L-fucono-1,5-lactone with the formation of reduced nicotinamideadenine dinucleotide phosphate (NADPH) (1).
(L-fucose dehydrogenase) (1)
L-Fucose + NADP+ --> L-fucono-1,5-lactone + NADPH + H+
The amount of NADPH formed in this reaction is stoichiometric with the amount of L-fucose. It is the NADPH which is measured by the increase in absorbance at 340 nm.
Biological Functions
L-(?)-Fucose is a deoxyhexose monosaccharide found on N- and O-linked glycans and glycolipids of a wide variety of organisms. It can exist as a terminal modification of glycan structures or serve as a point of attachment for adding other sugars. In humans, L-(?)-Fucose plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.
Biological Activity
L-Fucose (6-Deoxy-L-galactose) is used in studies of fucoidan polysaccharides containing glycans. It is studied as a glycan modifying carbohydrate that generates antigenic sites recognized by IgE antibodies. It is used as a substrate to identify, differentiate, and characterize enzymes such as fucosidase(s),l-fucose isomerase(s), and L-fucose dehydrogenase(s). It may be used to study organelles, and bacterial microcompartments, involved in the degradation of plant and algal cell wall sugars. L-Fucose may also be used as a reference compound in rare sugar identification and analysis.
